Richmond loses experienced players - such as George Smith (retired), and Arthur “Bolivar” Powell, Harry Eldridge, and Dunn (to other clubs).
Richmond is generally seen as inexperienced and light.
No second twenty is formed this year.

May Sat. 4 Richmond lose to South Melbourne by ten goals before 6,000 spectators at South. South wear their blue 1888 premiership caps.

Wed. 8A football match on roller skates, involving men and women, is played between teams from the districts of Richmond and Fitzroy. It was a part of a skating carnival on the Richmond Skating Rink. Neither team scores.

Sat. 25Richmond plays its second game in two days. It defeats Fitzroy having drawn with Melbourne the day earlier on Queens Birthday.

Fri. 31Colden Harrison, an early football administrator and player who captained the first Richmond Football Club in 1861 is one of four people honoured with the first VFA life memberships.

JuneSat. 1Footscray play the first half of its game against Richmond with only 18 men. They were apparently unaware of this handicap and following its discovery played with a full team of 20.

Mon. 3A special meeting of Richmond players, officials and members is held at Wookey Bros. shop. Prominent bookmaker and avid South Melbourne supporter Robert Phillips presents Billy Brown with a gold medal for being, “the most successful goal kicker of the last season.”

Sat 15Richmond plays against a South Australian club for the first time. Port Adelaide 8 - 2 defeats Richmond 7 - 15 on the RCG.

Sat. 22 Harry Trowbridge, who played in Richmond’s first two games of 1889, appears for Melbourne against Richmond.

July Ground:
The Richmond Football Club and the Richmond Cricket Club argue over improvements to the press and spectator facilities at the RCG. The Sportsman writes that while the football club wants to improve the ground the cricket club has a “dog-in-a-manger” attitude.

Sat. 6Ballarat’s footballers, having defeated Richmond ten goals to one on the RCG, are stoned by Richmond larrikins as they entered their cabs.

Sat. 13 Jack Stewart represents Victoria against Northern New South Wales at the MCG.
Richmond plays St. Kilda today despite the conflict with the inter-colonial game. St. Kilda needed to play this game in order to play the minimum number of games to qualify for the premiership.
“Yellow and Black”, writing in The Richmond Guardian, refers to the game against Ballarat taking place on “the local ground at Punt-road”. On August 10, 1889, “Yellow and Black” referred to the Essendon game being played “at Punt road”. But this geographical reference would remain rare in the nineteenth century, the ground was generally known as the Richmond ground, or in the Richmond press as the “local cricket ground”.

AugustThr. 1 The Box Hill Reporter’s football columnist calls for East Richmond’s dismissal from the Victorian Junior FA if they “... can not play a more gentlemanly game”.

Sat. 10 Richmond’s ten goals against Footscray at the RCG equals the club record for the most goals in a senior premiership game.

SeptemberFri. 6 Only thirteen of the regular team appear at Spencer-street station for Saturday’s game against Ballarat at Ballarat. Jimmy Eastman who was entrusted to manage the team hastily telegraphed for men and locates some last minute substitutes.

Sat. 7South Ballarat defeats Richmond nine goals to nil at Saxon Paddock. A Billy Brown “goal” was called back by the umpire. The game was rough with a Richmond player anxious to fight his opponent after the three-quarter time bell rang.

Sat. 14 In the last quarter Richmond kicks four goals in twelve minutes to defeat Footscray five goals to two.

Sat. 28South Melbourne defeats Richmond 13 - 9 to 0 - 6 on the RCG before 5,000 spectators. It is not only the largest score yet kicked on the RCG, the win secured the 1889 premiership for South Melbourne.

Juniors:East Richmond are runners up to North Park in the Victorian Junior FA premiership. Alf. Elder is the club’s leading goal kicker with 18.